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1.  4-(4-Chloro­phen­yl)-2,6-bis­(1H-indol-3-yl)-1,4-dihydro­pyridine-3,5-dicarbo­nitrile ethanol monosolvate 
In the title compound, C29H18ClN5·C2H6O, the dihydro­pyridine ring adopts a strongly flattened envelope conformation, with a maximum deviation of 0.139 (2) Å from its best plane for the Csp 3 atom. The dihedral angles between the dihydro­pyridine ring plane and the two indole rings in positions 2 and 6 are 34.28 (5) and 40.50 (6)°, respectively. In turn, the benzene ring and the dihydro­pyridine ring are oriented at a dihedral angle of 74.69 (6)°. An intra­molecular C—H⋯Cl hydrogen bond occurs. In the crystal, mol­ecules are linked by N—H⋯N, N—H⋯O and O—H⋯N hydrogen bonds into layers parallel to (001). There are short C—H⋯Cl contacts between mol­ecules in neighboring layers.
PMCID: PMC3344446  PMID: 22590208
2.  Ethyl 6-amino-8-(4-chloro­phen­yl)-9-nitro-2,3,4,8-tetra­hydro­pyrido[2,1-b][1,3]thia­zine-7-carboxyl­ate 
In the structure of the title compound, C17H18ClN3O4S, the thia­zinane ring displays a twist-boat conformation. The 1,4-dihydro­pyridine ring is approximately perpendicular to the benzene ring [dihedral angle = 88.3 (1)°]. The mol­ecular conformation is stabilized by an intra­molecular N—H⋯O hydrogen bond. In the crystal, mol­ecules are linked by N—H⋯O inter­actions into a C(8) chain along [100].
PMCID: PMC3200856  PMID: 22058968
3.  2′-Amino-1′-(4-chloro­phen­yl)-1,7′,7′-trimethyl-2,5′-dioxo-5′,6′,7′,8′-tetra­hydrospiro­[indoline-3,4′(1′H)-quinoline]-3′-carbonitrile dimethyl­formamide solvate dihydrate 
In the mol­ecule of the title compound, C26H23ClN4O2·C3H7NO·2H2O, the indole and dihydro­pyridine rings are planar and make a dihedral angle of 89.86 (7)°. The dihydro­pyridine ring forms a dihedral angle of 79.95 (7)° with the attached benzene ring. In the crystal structure, inter­molecular N—H⋯O and O—H⋯O hydrogen bonds link the mol­ecules. Intermolecular C—H⋯N and C—H⋯Cl interactions are also present.
PMCID: PMC2968848  PMID: 21582586
4.  N-[2-({[1-(4-Chloro­phen­yl)-1H-pyrazol-3-yl]­oxy}meth­yl)phen­yl]-N-meth­oxy­hydrazinecarboxamide 
In the title compound, C18H18ClN5O3, the hydrazinecarboxamide N—N—C(O)—N unit is nearly planar [maximum deviation = 0.074 (2) Å] and is inclined at a dihedral angle of 57.43 (7)° with respect to the plane of the attached benzene ring. The chloro­phenyl group makes dihedral angles of 19.71 (7) and 34.07 (6)° with the pyrazole and benzene rings, respectively. In the crystal, pairs of N—H⋯O hydrogen bonds link the mol­ecules into inversion dimers that are further linked into chains along the a-axis direction by N—H⋯N hydrogen bonds. In addition, π–π stacking inter­actions are observed between benzene rings [centroid–centroid distance = 3.680 (1) Å].
PMCID: PMC3470263  PMID: 23125707
5.  5-(4-Chloro­phen­yl)-1-methyl-3-phenyl-3,6,8,9-tetra­hydro­pyrazolo­[3,4-b]thio­pyrano[4,3-d]pyridine 
The title compound, C22H18ClN3S, was synthesized by the reaction of 4-chloro­benzaldehyde, tetra­hydro­thio­pyran-4-one and 3-methyl-1-phenyl-1H-pyrazol-5-amine in acetic acid without a catalyst. The pyridine and pyrazole rings are almost coplanar, the dihedral angle between their mean planes being 2.50 (1)°. The thio­pyran ring exhibits an envelope conformation. The crystal packing is stabilized by inter­molecular C—H⋯Cl hydrogen bonds and by C—H⋯π and π–π inter­actions [centroid–centroid distances of 3.825 (2) Å between pyridine rings and 3.557 (2) Å between pyrazole and pyridine rings.
PMCID: PMC3200927  PMID: 22059005
6.  4-[2-(4-Chloro­phen­yl)hydrazinyl­idene]-3-methyl-1H-pyrazol-5(4H)-one 
In the title compound, C10H9ClN4O, the pyrazole ring [maximum deviation = 0.014 (2) Å] forms a dihedral angle of 7.06 (14)° with the chloro­benzene ring. The mol­ecular conformation is stabilized by an intra­molecular N—H⋯O hydrogen bond, which generates an S(6) ring motif. In the crystal, inversion dimers linked by pairs of C—H⋯O hydrogen bonds generate R 2 2(16) ring motifs. The dimers are further connected by N—H⋯N hydrogen bonds, thereby forming layers lying parallel to the bc plane.
PMCID: PMC3201479  PMID: 22058782
7.  9-(3-Bromo-5-chloro-2-hy­droxy­phen­yl)-10-(2-hy­droxy­eth­yl)-1,2,3,4,5,6,7,8,9,10-deca­hydro­acridine-1,8-dione 
In the title compound, C21H21BrClNO4, the dihydro­pyridine ring adopts a flattened boat conformation. The 3-bromo-5-chloro-2-hy­droxy­phenyl ring forms a dihedral angles of 84.44 (7)° with the dihydro­pyridine mean plane. The mol­ecular conformation is stabilized by an intra­molecular O—H⋯O hydrogen bond, with an S(8) ring motif. In the crystal, O—H⋯O and C—H⋯O hydrogen bonds link the mol­ecules, forming a three-dimensional network.
PMCID: PMC3588342  PMID: 23476467
8.  (Z)-1-(2-Chloro­phen­yl)-3-methyl-4-[2-(4-nitro­phen­yl)hydrazin-1-yl­idene]-1H-pyrazol-5(4H)-one 
There are two independent mol­ecules, A and B, in the asymmetric unit of the title compound, C16H12ClN5O3. The relative orientations of the chloro­phenyl ring with respect to the pyrazole ring in the two crystallographically independent mol­ecules are different, and their corresponding dihedral angles are −53.3 (2) and 114.09 (18)° in mol­ecules A and B, respectively. There are two strong intramolecular N—H⋯O hydrogen bonds, and two weak intramolecular C—H⋯O and C—H⋯Cl hydrogen bonds. The crystal packing is constructed by weak C—H⋯O and N—H⋯O inter­actions, and two π–π stacking inter­actions [centroid–centroid distances = 3.7894 (9) and 3.5719 (10) Å], forming a mol­ecular ladder along the a axis.
PMCID: PMC3414286  PMID: 22904819
9.  Diethyl 4-[2-(4-meth­oxy­phen­yl)-1H-pyrazol-3-yl]-2,6-dimethyl-1,4-dihydro­pyridine-3,5-dicarboxyl­ate 
In the title compound, C23H27N3O5, the pyrazole ring is inclined at dihedral angles of 38.16 (6) and 80.80 (6)°, respectively, to the least-squares planes of the benzene and dihydro­pyridine rings. In the crystal, adjacent mol­ecules are linked via a pair of N—H⋯N hydrogen bonds, forming an inversion dimer. The dimers are stacked in a column along the a axis through N—H⋯O hydrogen bonds. Intra- and inter­molecular C—H⋯N and C—H⋯O hydrogen bonds are also observed.
PMCID: PMC3120286  PMID: 21754799
10.  [3-(4-Chloro­phen­yl)-5-hydr­oxy-5-phenyl-4,5-dihydro-1H-pyrazol-1-yl](3-pyrid­yl)methanone 
In the title compound, C21H16ClN3O2, the dihedral angles formed by the pyrazole ring with the pyridyl, phenyl­ene and phenyl rings are 6.80 (5), 9.23 (5) and 74.96 (5)°, respectively. The phenyl and phenyl­ene rings are inclined at 80.14 (2)°. Intra­molecular O—H⋯O and C—H⋯N hydrogen bonds generate S(6) ring motifs. The crystal packing is strengthened by short inter­molecular O—H⋯N, C—H⋯O hydrogen bonds and π–π stacking inter­actions with centroid–centroid distances of 3.6247 (5)–3.7205 (5) Å, together with inter­molecular short O⋯N contacts [2.7682 (11) Å]. Mol­ecules are linked into infinite chains along [100].
PMCID: PMC2959893  PMID: 21581336
11.  1-[3-(4-Chloro­phen­yl)-5-(4-meth­oxy­phen­yl)-4,5-dihydro-1H-pyrazol-1-yl]butan-1-one 
In the title compound, C20H21ClN2O2, the benzene rings form dihedral angles of 6.35 (5) and 81.82 (5)° with the mean plane of the 4,5-dihydro-1H-pyrazole ring (r.m.s. deviation = 0.145 Å). This latter ring adopts an envelope conformation with the CH grouping as the flap. The dihedral angle between the benzene rings is 75.63 (4)°. In the crystal, mol­ecules are linked by C—H⋯Cl and C—H⋯O hydrogen bonds into chains along [-201]. The crystal structure also features C—H⋯π inter­actions.
PMCID: PMC3343949  PMID: 22590030
12.  N-(4-Chloro­phen­yl)-5-(4,5-dihydro-1H-imidazol-2-yl)thieno[2,3-b]pyridin-4-amine 
In the title compound, C16H13ClN4S, the thienopyridine fused-ring system is nearly planar (r.m.s. deviation = 0.0333 Å) and forms a dihedral angle of 4.4 (3)° with the attached dihydro­imidazole ring (r.m.s. deviation = 0.0429 Å) allowing for the formation of an intra­molecular (exocyclic amine)N—H⋯N(imine) hydrogen bond. The benzene rings of the disordered (50:50) –N(H)—C6H4Cl residue form dihedral angles of 59.1 (3) and 50.59 (15)° with the fused ring system. In the crystal, (imidazole amine)N—H⋯N(pyridine) hydrogen bonds lead to a supra­molecular helical chain along the b axis. The chains assemble into layers (ab plane) with inter-digitation of the chloro­benzene rings which results in weak C—H⋯Cl inter­actions in the c-axis direction.
PMCID: PMC3393946  PMID: 22798811
13.  1-[3-(4-Chloro­phen­yl)-5-(4-meth­oxy­phen­yl)-4,5-dihydro-1H-pyrazol-1-yl]ethanone 
In the title compound, C18H17ClN2O2, the benzene rings form dihedral angles of 6.69 (6) and 74.88 (5)° with the 4,5-dihydro-1H-pyrazole ring. The benzene rings form a dihedral angle of 76.67 (5)° with each other. In the crystal, mol­ecules are linked via bifurcated (C,C)–H⋯O hydrogen bonds into chains along [010]. The crystal structure is further consolidated by C—H⋯π inter­actions.
PMCID: PMC3343987  PMID: 22589896
14.  4-[5-(4-Chloro­phen­yl)-3-methyl-1H-pyrazol-1-yl]benzene­sulfonamide 
In the title compound, C16H14ClN3O2S, the dihedral angle between the benzene and pyrazole rings is 52.75 (2)°, while that between the pyrazole and 4-chloro­phenyl rings is 54.0 (3)°. The terminal sulfonamide group adopts an approximately tetra­hedral geometry about the S atom with a C—S—N angle of 108.33 (10)°. In the crystal, pairs of N—H⋯N hydrogen bonds lead to the formation of inversion dimers. These dimers are linked via a second pair of N—H⋯N hydrogen bonds and C—H⋯O interactions, forming a two-dimensional network lying parallel to the bc plane. The two-dimensional networks are linked via C—H⋯Cl interactions, forming a three-dimensional structure.
PMCID: PMC3569817  PMID: 23424563
15.  1-[5-(2-Chloro­phen­yl)-5-hy­droxy-3-methyl-4,5-dihydro-1H-pyrazol-1-yl]­ethanone 
The title compound, C12H13ClN2O2, crystallizes with two independent but very similar mol­ecules (A and B) in the asymmetric unit. The pyrazole ring in each mol­ecule has an envelope conformation. The dihedral angle between the pyrazole ring mean plane and the benzene ring is 86.07 (14)° in A and 85.99 (14)° in B. In the crystal, the A and B mol­ecules are linked via a pair of O—H⋯O hydrogen bonds, forming dimers. These dimers are further linked via C—H⋯O inter­actions to form –A–B–A–B– chains propagating along the c-axis direction.
PMCID: PMC3297897  PMID: 22412700
16.  N-(3-Chloro­phen­yl)-3-nitro­pyridin-2-amine 
The dihedral angle between the benzene and pyridyl rings in the title compound, C11H8ClN3O2, is 22.65 (10)°, indicating a twisted mol­ecule. The amine H and nitro O atoms form a donor–acceptor pair for an intra­molecular N—H⋯O hydrogen bond so that the nitro group is almost coplanar with the pyridine ring to which it is connected [O—N—C—C torsion angle = 7.4 (3)°]. The pyridine N and Cl atoms are approximately syn. The crystal packing features C—H⋯Cl inter­actions that lead to undulating supra­molecular chains along [101]. These are connected into sheets by π–π inter­actions occurring between the benzene rings and between the pyridine rings of translationally related mol­ecules along the b axis [centroid–centroid distances = length of b axis = 3.7157 (2) Å].
PMCID: PMC3247465  PMID: 22220083
17.  [1-(4-Chloro­phen­yl)-5-hy­droxy-3-phenyl-1H-pyrazol-4-yl](thio­phen-2-yl)methanone 
In the title compound, C20H13ClN2O2S, the chloro­phenyl, phenyl and thienoyl rings are oriented at dihedral angles 17.84 (7), 53.13 (8) and 34.03 (8)°, respectively, to the central pyrazole ring. An intra­molecular O—H⋯O hydrogen bond occurs. In the crystal, pairs of bifurcated O—H⋯O hydrogen bonds link mol­ecules into inversion dimers with R 2 2(12) graph-set motifs.
PMCID: PMC3379242  PMID: 22719440
18.  (4-Chloro­phen­yl)[1-(4-methoxy­phen­yl)-3-(5-nitro-2-fur­yl)-1H-pyrazol-4-yl]methanone 
In the title compound, C21H14ClN3O5, an intra­molecular C—H⋯O hydrogen bond generates an S(7) ring motif and the furan and pyrazole rings are almost coplanar, making a dihedral angle of 1.98 (5)°. The pyrazole ring is inclined at dihedral angles of 47.59 (4) and 7.27 (4)° to the chloro­phenyl and methoxy­phenyl groups, respectively. The nitro group is almost coplanar to its attached furan ring [dihedral angle = 2.03 (12)°]. In the crystal, inter­molecular C—H⋯O hydrogen bonds link the mol­ecules into a three-dimensional network. The crystal structure also features short inter­molecular O⋯N [2.8546 (12) Å] and Cl⋯O [3.0844 (9) Å] contacts as well as aromatic π–π stacking inter­actions [centroid–centroid distance = 3.4367 (6) Å].
PMCID: PMC2979246  PMID: 21579120
19.  3-(4-Chloro­phen­yl)-1-phenyl-1H-pyrazole-4-carbaldehyde 
In the title compound, C16H11ClN2O, the chloro-substituted phenyl ring is disordered over two positions with refined site occupancies of 0.503 (2) and 0.497 (2). The dihedral angle between the pyrazole and phenyl rings is 7.93 (7)°. The pyrazole ring also forms dihedral angles of 24.43 (9)° and 28.67 (9)° with the disordered chloro-substituted benzene ring. In the crystal, mol­ecules are linked by inter­molecular C—H⋯O hydrogen bonds, generating R 2 1(7) and R 2 2(10) ring motifs. π–π inter­actions between the pyrazole and phenyl rings [centroid–centroid distance = 3.758 (1) Å] further stabilize the crystal structure.
PMCID: PMC3151838  PMID: 21837157
20.  Dimethyl 4-[3-(4-meth­oxy­phen­yl)-1-phenyl-1H-pyrazol-4-yl]-2,6-dimethyl-1,4-dihydro­pyridine-3,5-dicarboxyl­ate dihydrate 
In the title compound, C27H27N3O5·2H2O, the dihydro­pyridine ring adopts a flattened boat conformation. The central pyrazole ring is essentially planar [maximum deviation of 0.003 (1) Å] and makes dihedral angles of 50.42 (6) and 26.44 (6)° with the benzene rings. In the crystal, mol­ecules are linked via N—H⋯O, O—H⋯O, O—H⋯N and C—H⋯O hydrogen bonds into two-dimensional networks parallel to the bc plane. The crystal structure is further consolidated by weak C—H⋯π inter­actions.
PMCID: PMC3394006  PMID: 22798871
21.  4-(4-Chloro­phen­yl)-3-cyano-7-(4-meth­oxy­phen­yl)-5-oxo-5,6,7,8-tetra­hydro-4H-chromen-2-aminium methano­late 
In the cation of the title organic ion pair compound, C23H20ClN2O3 +·CH3O−, the cyclo­hexyl ring shows a half-boat conformation and the dihedral angles between two benzene rings and the pyran ring are 83.14 (7) and 73.18 (9)°. In the crystal, centrosymmetrically related cations are linked into a dimer by pairs of N—H⋯N hydrogen bonds, generating an R 2 2(12) ring motif. The anion inter­acts with the dimer through an N—H⋯O hydrogen bond. π–π inter­actions between pyran rings of adjacent dimers, with a centroid–centroid distance of 3.861 (2) Å, are also observed.
PMCID: PMC3297885  PMID: 22412688
22.  4-{2-[2-(4-Chloro­benzyl­idene)hydrazinyl­idene]-3,6-dihydro-2H-1,3,4-thia­diazin-5-yl}-3-(4-meth­oxy­phen­yl)sydnone 
The title compound, C19H15ClN6O3S, exists in trans and cis configurations with respect to the acyclic C=N bonds. The 3,6-dihydro-2H-1,3,4-thia­diazine ring adopts a half-boat conformation. The sydnone ring is approximately planar [maximum deviation = 0.013 (1) Å] and forms dihedral angles of 34.76 (4) and 48.67 (4)° with the benzene rings. An intra­molecular C—H⋯O hydrogen bond stabilizes the mol­ecular structure and forms an S(6) ring motif. In the crystal packing, inter­molecular N—H⋯N hydrogen bonds link centrosymmetrically related mol­ecules into dimers, generating R 2 2(8) ring motifs. The dimers are then linked into a three-dimensional network by inter­molecular C—H⋯O and C—H⋯Cl hydrogen bonds, and by C—H⋯π inter­actions. Further stabilization is provided by π–π inter­actions involving the sydnone rings, with centroid–centroid separations of 3.4198 (5) Å.
PMCID: PMC3089192  PMID: 21754480
23.  10-(4-Chloro­phen­yl)-9-(4-fluoro­phen­yl)-3,3,6,6-tetra­methyl-3,4,6,7,9,10-hexa­hydro­acridine-1,8(2H,5H)-dione 
The title compound, C29H29ClFNO2, was synthesized by the reaction of 4-fluoro­benzaldehyde, 5,5-dimethyl­cyclo­hexane-1,3-dione and 3-(4-chloro­phenyl­amino)-5,5-dimethyl­cyclo­hex-2-enone in an ionic liquid (1-butyl-3-methyl­imidazolium bromide). X-ray analysis reveals that the 1,4-dihydro­pyridine ring adopts a boat conformation, while each of the attached partially saturated six-membered rings adopts a half-chair conformation. The structure is stabilized by weak C—H⋯O and C—H⋯F hydrogen bonds. The mol­ecule has approximate mirror symmetry; the largest deviation from this symmetry concerns the fluoro- and chloro­phenyl rings.
PMCID: PMC2960627  PMID: 21201754
24.  1-(4-Chloro­phen­yl)-4,4,6-trimethyl-3,4-dihydro­pyrimidine-2(1H)-thione 
The dihydro­pyrimidine ring of the title compound, C13H15ClN2S, adopts an envelope conformation with five almost coplanar atoms (r.m.s. deviation = 0.054 Å) and the C atom bearing the two methyl substituents deviating from this plane by 0.441 (2) Å. The best plane through the five almost coplanar atoms forms a dihedral angle of 89.56 (5)° with the benzene ring. The crystal packing is characterized by centrosymmetric dimers connected by pairs of N—H⋯S hydrogen bonds.
PMCID: PMC2979773  PMID: 21579855
25.  (E)-3-(4-Chloro­phen­yl)-3-[3-(4-chloro­phen­yl)-1H-pyrazol-1-yl]prop-2-enal 
In the title compound, C18H12Cl2N2O, the pyrazole ring is almost planar [r.m.s. deviation = 0.002 Å] while the two chloro­phenyl rings are twisted out from the plane of the pyrazole ring, making dihedral angles of 5.3 (1) and 65.34 (4)°. In the crystal, centrosymmetric R 2 2(24) dimers are formed about crystallographic inversion centres through a pair of C—H⋯Cl inter­actions. These dimers are further linked through a C—H⋯O hydrogen bond, forming a C(8) chain extending along the a axis. C—H⋯π inter­actions are also observed.
PMCID: PMC2983380  PMID: 21587573

Results 1-25 (79870)